Use of solid carrier for dyeing hydrophobic fibers

ABSTRACT

A process of coloring a hydrophobic fiber with a disperse or cationic dyestuff is disclosed using a dye carrier composition containing a carrier which is a solid at a temperature of at least 45*C in conjunction with a compound of the formula:

United States Patent [1 1 Dellian et al.

[451 Apr. 15, 1975 USE OF SOLID CARRIER FOR DYEINO HYDROPHOBIC FIBERSAssignee:

Filed:

Inventors: Kurt A. Dellian, Spring Valley;

Marvin Weiskopf, Bronx, both of N.Y.; Samuel Lee, Fairlawn, NJ.

Ciba-Geig y Corporation, Ardsley,

Jan. 4, 1974 Appl. No.: 431,008

Related U.S. Application Data Division of Ser. No. 215,097, Jan. 3,1972, Pat. No.

U.S. Cl. 8/ 2; 8/173;8/174 Int. Cl C09b 67/00 Field of Search 8/92, 169,173, 174;

References Cited UNITED STATES PATENTS Sertorio Musser et al.

Stirton et al. 252/354 X 4/1971 Foley 252/354 X 4/1973 Freshwater et a].8/174 OTHER PUBLICATIONS Schwartz et al., Surface Active Agents, 1949,p. 51, lnterscience Publishers, Inc., N.Y., N.Y., TP 14953C3.

[57] ABSTRACT A process of coloring a hydrophobic fiber with a disperseor cationic dyestuff is disclosed using a dye carrier compositioncontaining a carrier which is a solid at a temperature of at least 45Cin conjunction with a compound of the formula:

I c(cH cooa cn dcn 5 Claims, No Drawings USE OF SOLID CARRIER FOR DYEINGHYDROPI'IOBIC FIBERS This is a Divisional of application Ser. No.215,097, filed Jan. 3, 1972, now US. Pat. No. 3,820,952.'

This invention concerns a dye carrier composition and the processutilizing such carrier composition for the coloring of synthetichydrophobic fibers.

It is well known that many synthetic fibers because of the hydrophobicproperties of the polymers which comprise them are difficult to colorwith dyestuffs following the usual dyeing methods.

Hydrophobic fibers such as polyethylene terephthalate, polyamides.cellulose triacetate, and the like however have been readily dyed withdisperse dyestuffs. Initially such dyeing was carried out under pressureat temperatures generally in excess of 250F. Such conditions addedgreatly to the cost and complexity of the dyeing process because of theequipment which was required. These difficulties have been reduced bythe utilization of dyeing auxiliaries known as carriers which facilitatethe penetration of the fiber by the dyestuff by causing a swelling ofthe fiber.

The use of carriers in the dyeing of hydrophobic fibers has resulted inthe realization of satisfactory dyeings at temperatures of 200-210F inunpressurized equipment in many instances. Among the typical carriersused by the art up to the present time are various derivatives ofbenzene and phenol such as orthoand para-phenylphenol, chlorinatedbenzenes, xylenes, naphthalenes, toluenes, aromatic esters or ethers,and biphenyl.

The use of carriers by those in the art has greatly improved thecapability to achieve satisfactory colorings.

and functions to essentially eliminate the dispersibility and stabilityproblem. The constituent is of the formula:

Y .is H, OH, SO H, OSO H, or the the alkali salt thereof such as sodium;

R is C,,H and n is an integer from 1 to 5, preferably 5 A desirableexample of the above compound is when 20 .r is 7, m is 7, Z is OSO H, Yis H and n is 5.

The carrier composition is utilized in the form of an emulsion which isadded to the dyebath formulation, printing paste or prescouring bath.The solid carrier will be employed at to 92 parts by weight to 8 to 90parts by weight of the disclosed constituent.

In the carrier composition various additives may be employed. A suitableexample is a sulfated alkylphenoxy polyethylene oxide or sodium saltwherein the alkyl 0 group contains-6 to carbon atoms such as 6 to 15However the capability to achieve satisfactorily stable emulsions ordispersions especially with solid carriers, in many respects has provenat times to be less than satisfactory. For example. a carrier which isinitially a solid may introduce a low degree of dispersibility in thedye liquor causing specks and carrier stains on the fabric. When thesolid carrier is compounded as a selfemulsifiable powder or paste, a lowdegree of stability may result.

Among the purposes of the present invention is to provide a new carriercomposition for use in the process of coloring hydrophobic fibers suchas polyesters, like polyethylene terephthalate solid under trademarkssuch as Dacron, Terylene and Fortrel, cellulose triacetates, polyamidesand the like.

The carrier composition of the present invention is useful in coloringfibers with both disperse and cationic dyestuffs. For example, it is'especially useful in coloring acid modified polyethylene terephthalate(Dacron) with cationic dyestuffs.

The carrier compound in the present composition will be a solid atnormal room temperature and temperatures at least as high as C. The termcarrier is employed in its normal terminology in the art and encompassesdyeing auxiliaries which facilitate the penetration of a hydrophobicfiber by a dyestuff by causing a swelling of the fiber. As previouslyset forth the dyestuffs contemplated in conjunction with carriercomposition includes disperse or cationic types.

Useful solid carrier components in the present disclosure includeo-phenylphenol, biphenyl, phenyl benzoate, phenyl salicylate andnaphthalene.

In conjunction with the solid carrier component as defined herein isused a constituent which is critical carbon atoms. A desirable additiveis the sodium salt of sulfated nonyl phenoxy (polyethylenoxy) ethanol.

A desirable carrier composition containing this latter additive is amixture containing to parts by weight of the solid carrier such asphenyl benzoate, 3 to 10 parts by weight of the disclosed constituent ofthe formula:

l c c {ca coon cH (cH of hydrophobic fibers by contacting the fiberswith from about 0.5 to about 20 parts of the carrier of the inventionper parts of the fibers by weight and maintaining the fibers in contactwith the carrier composition a disperse or cationic dyestuff and at atemperature and for a period of time sufficient to color the fiber. Apreferred amount of carrier to employ is considered to be from 0.5 to 6parts per 100 parts of fiber by weight. Generally temperatures of 200 to210F will be employed.

The term fiber as used herein is meant to include filaments, bristlesand fabrics and the like. It is not applicable to films and/or foils.

The process of coloring as used herein is meant to include both printingand dyeingusing all the usual methods employing carriers familiar tothose skilled in the art. Both roller printing and screen printing aretherefore included as well as dyeing by the beck, jig, padder, and otherwell known dyeing methods.

To further illustrate the innovative aspects the following examples areprovided:

EXAMPLE I I on 4 OZO based on the dry weight of 100 parts Dacronpolyethylene terephthalate fabric. The fabric is loaded in a beck at aliquor ratio of 30:1, run for minutes at 40C, and the temperature thenis raised over 30 minutes to the boil and maintained at the boil for onehour.

A very satisfactory yellow shade is obtained.

EXAMPLE 2 The procedure of Example I is repeated but employing 3 partsby weight of a dyestuff of the formula:

SO CH OEN N-NEO N C l-MON A strong reddish brown shade of excellentlight fastness is obtained.'

EXAMPLE 3 A printing paste is prepared containing 10 parts of thecarrier composition described in Example 1, 2.5 parts of a dyestuff ofthe formula:

3 parts alignate thickener, and 20 parts mineral spirits.-

A polyethylene terephthalate cloth is printed with the paste and thenthe printed cloth is cured for one minute at 35090F. The cloth is thensoaped and rinsed. A

vivid reddish blue shade is obtained.

EXAMPLE 4 Following the general procedure of Example 1. a fabric of acidmodified polyethylene terephthalate (Dacron 64) is dyed using 1.5 partsof a dyestuff of the formula:

c-cn 3 7 a n-CHTCH@ \c mcn A brilliant pink shade having good fastnessproperties is obtained.

EXAMPLE 5 The procedure of Example l is repeated but employing 2.5 partsof the dyestuff of the formula:

OCI-I O OH and 6 parts of the carrier emulsion composition A vividpinkshade of excellent fastness is obtained,

EXAMPLE 6 A dye carrier composition is prepared by emulsifying 65 partsby weight of biphenyl with 15 parts of sodium I oleylbutylsulfate and 20parts of water. 12 lbs. of the emulsionthus formed are added to adyebath at C containing 1.5 lbs. of the disperse dye of the formula:

in a liquour ratio of 40:1 in a dye bath with 100 pounds of polyethyleneterephthalate (Dacron 54)' fabric at l40F. The temperature is raised toboiling over a period of 20 minutes and then maintained at boiling for90 minutes. The fabric is rinsed, soaped, and placed in a bath of 2%hydrosulfite and 2% by weight soda ash for 15 minutes at 180F. Abrilliant yellow shade having excellent fastness properties results.

EXAMPLE 7 Fifty pounds of polyethylene terephthalate knitted fabric isprescoured at boiling temperatures in a beck with a bath containing 6%by weight of the emulsion prepared in Example 6 for a period of 45minutes. The scouring bath is removed, and the fabric rinsed with coldwater. The fabric is then dyed in a bath containing 3 parts by weight ofa disperse dyestuff of the formula:

' C2H4CN \CZHS starting at l60F and raising the temperature to boilingover 30 minutes. Boiling is maintained by 1 hour. The fabric is thenrinsed and treated with the hydrosulfite/- soda ash bath as in Example6. A deep brown-red shade having excellent fastness properties results.

EXAMPLE 8 The procedure of Example 6 is repeated but employing thedyestuff of the formula:

v CH3 OCH A very fast deep orange shade results.

EXAMPLE 9 The procedure of Example 6 is repeated but employ-' ing onepart of the dyestuff of the formula:

0 N (CH2) 3 NH CO A blue shade of good fastness results.

EXAMPLE ID The procedure of Example 7 is repeated but using a mixturecomprising two parts each of the compounds of the following formula:

l i /OCi O and O OH 10 O Cl-l A brilliant violet shade of excellentfastness results.

EXAMPLE I l The procedure of Example 1 is repeated but with thefollowing carrier composition: 70 parts phenyl benzoate 9 parts sodiumnonyl phenyl poly(ethylenoxy) ethanol sulfate 4.5 parts sodium oleylamylester sulfate 5 parts ethylene glycol l 1.5 parts water While theinvention has been described with particular reference to specificembodiments, it is to be understood that it is not to be limited theretobut is to be construed rather broadly within the scope and extent of theappended claims.

What is claimed is: l. A carrier composition useful in coloringsynthetic hydrophobic fibers containing 10 to 92 parts by weight of acarrier selected from the group consisting of ophenylphenol, biphenylphenyl benzoate. phenyl salicylate, naphthalene and mixtures thereofwhich is solid to a temperature of at least C and 8 to parts by weightof a compound of the formula:

Z is SO H or OSO H; Y is H, OH, SO H, or OSO H; and R is C,,H and n isan integer from 1 to 5.

5. A carrier composition useful in coloring synthetic hydrophobic fiberscontaining 50 to 90 parts by weight of phenyl benzoate, 3 to 10 parts byweight of the amylester of the sodium salt of sulfonated oleic acid and5 to 20 parts by weight of the sodium salt of sulfated nonylphenoxy poly(ethylenoxy) ethanol.

1. A CARRIER COMPOSITION USEFUL IN COLORING SYNTHETIC HYDROPHOBIC FIBERSCONTAINING 10 TO 92 PARTS BY WEIGHT OF A CARRIER SELECTED FROM THE GROUPCONSISTING OF O-PHENYLPHENOL, BIPHENYL PHENYL BENOATE, PHENYLSALICYLATE, NAPHTHALENE AND MIXTURES THEREOF WHICH IS SOLID TO ATEMPERATURE OF AT LEAST 45*C AND 8 TO 90 PARTS BY WEIGHT OF A COMPOUNDOF THE FORMULA:
 2. The carrier composition of claim 1 which contains 50to 90 parts by weight of the solid carrier and 5 to 10 parts by weightof said compound.
 3. The carrier composition of claim 2 wherein x is 7,m is 7, Z is OSO3H, Y is H and n is
 5. 4. The carrier composition ofclaim 2 containing 10 to 20 parts by weight of sulfated alkylphenoxypolyethylene oxide or salt thereof.
 5. A carrier composition useful incoloring synthetic hydrophobic fibers containing 50 to 90 parts byweight of phenyl benzoate, 3 to 10 parts by weight of the amylester ofthe sodium salt of sulfonated oleic acid and 5 to 20 parts by weight ofthe sodium salt of sulfated nonylphenoxy poly (ethylenoxy) ethanol.